Harry was Charlie Jolson's right-hand man, and was often seen wielding a sawn-off shotgun throughout the story. Harry was extremely loyal to Charlie and was rarely seen without him. Harry would help Charlie out by driving him around London and making phone calls for him in his absence. Harry was involved in the kidnapping of Mark Hammond's son, Alex, and was assisted by Yasmin. He shot Suzie when she resisted being kidnapped. He was later killed by Mark Hammond aboard the Sol Vita.

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Harry was born in Hackney, London in 1938. At a young age, he befriended Charlie Jolson, who was an associate of the Kray twins. In 1970, Harry became Charlie's second in command as they formed the Bethnal Green Mob that would later become London's most notorious gang.

By 2002, the Bethnal Green Mob's notoriety had fallen. They were no longer the most powerful gang in London as the Collins Gang, the Triads and the Yardies had become more powerful. Charlie Jolson made up a plan that would sort them out. As part of his plan, he was going to have Mark Hammond's wife and son kidnapped. Charlie knew that Mark had recently been released from prison. Charlie asked Harry to help out with the kidnapping and sent him along with Eyebrows, Yasmin and Grievous. Eyebrows asked Harry what they needed a girl like Yasmin for, but Harry explained that they needed a hitwoman because "things have a habit of getting complicated". As Suzie and Alex left the house, Harry along with Yasmin and Grievous confronted them. Yasmin and Suzie got in a fight and Harry along with Grievous had to restrain Suzie. However, Suzie resisted and Harry shot her. Harry would later comment that he thought that Suzie had a "nice 'arris". Unfortunately for Mark, Suzie died from her wounds, making Harry a murderer. Mark chased after the gang car and found them at a warehouse. Eyebrows and Grievous put Mark in a chair while Harry aimed his shotgun at Mark. Charlie told Mark that he now worked for them or else Alex will die. Harry later met Mark when he arrived at the Spotted Dog pub to give Charlie his statue back. However, Harry did not like Mark's attitude and gave him a kicking, after the pub landlord Reggie hit him over the head with a bottle. Grievous and Big Walter had to restrain Harry as Charlie needed Mark to carry out his mission. Harry later had to act as Mark's boss, while Charlie was busy. He gave Mark his mission briefing for the assassination of Clive McCormack. He later told Mark to get Layla, one of Charlie's girls and for him to bring her to Charlie's mansion. As Mark was frustrated with the Jolson's, Harry had to be sympathetic with Mark in order to get him to work. However, when Mark completed his missions and wanted his son back, Harry was no longer sympathetic. After Mark had betrayed Charlie, Harry referred to Mark as a "heap of shit".

As part of Charlie's plan to deal with Mark Hammond and all the other gangs in London, Harry drove Alex to the Sol Vita where he held him hostage. Mark broke out of his cell at Charlie's warehouse and drove to the Sol Vita to find Alex. Harry was confronted by Mark. Harry wanted to shoot Mark dead and then kill Alex so he had killed all of the Hammonds. During the confrontation, Harry antagonised Mark about Suzie's death. Mark eventually killed Harry, avenging Suzie's murder. After Harry's death, Mark informed Yasmin of his death.

Despite being old, Harry was aggressive and not shy about using violence. He seemed to hate Mark more than any other, including Jake and Charlie. Harry did, however, have a sympathetic side as he tried to be nice to Mark. However, this was to get Mark to co-operate and Harry did not care at all about Mark's personal feelings. Harry showed great loyalty towards Charlie Jolson and was always willing to help Charlie with anything, whatever the task was. Like Charlie, Harry is racist towards blacks as he referred to the Yardies as "baboons".

During Frank Carter's missions, Harry makes a non-speaking appearance in a cutscene in Show some Remorse. He also appears and speaks in a cutscene in Meet Mark Hammond, which was a 'behind the scenes' version of the cutscene from The Prodigal Son.

"Fucking manners!" - Harry to Mark as he kicks him after Mark threatens Charlie with a gun in Aiding and Abetting.

"So here's the drill: you do this job, you get your boy back. You fuck it up, he ends up in the river. It's that simple. How do you want to play it?" - Harry gives Mark an ultimatum in Filthy Business.

"You're in deep now, son, very deep. You're going to have to play very rough if you ever want to get out and see the boy." - Harry warns Mark of how he should proceed in Filthy Business.

"Shame. Not a bad piece of crumpet, but you know women, mate, too much hassle." - Harry talks about Mark supposedly having killed Yasmin in A Touch of Class.

"Your man Collins seems to have hired some dancing slut, goes by the name of Layla. She's one of Charlie's birds and he'd like you to politely ask her to come back." - Harry sarcastically instructs Mark about his next mission in A Touch of Class.

There is question as to whether it was Harry or Grievous who killed Suzie . Harry however was the one who shot and killed Suzie, and this is confirmed later when he mocks Mark on the Sol Vita by saying that he is going for a complete set of Hammond's. Having killed Suzie, he aims to kill Mark and then the boy. If you see accurately, in the mission The Frightener Harry is seen draw out a Glock 17 Pistol. Later Grievous is seen unarmed while grabs Suzie, and Harry ready to point the pistol to her

Although it was Harry who killed Suzie, Mark says that it is Charlie who owes him blood by killing his wife. Mark therefore believes Charlie to be the 'real murderer' of his wife. However, Mark may simply have been projecting his rage onto Charlie due to not knowing Harry was the one who pulled the trigger.

Most of times, in the mission Aboard the Sol Vita, Harry is already injured when you face him in the stage, even if you didn't shoot him earlier. The reason for this is unknown. It was probably done to make the mission more easy.

Harry and Hammond evidently have some bad history. Harry seems to take a dislike to Mark straight away and appears to hate him more than everyone else including Charlie and Jake. This hate can be seen when he beats Mark badly in the mission, Aiding and Abetting . Later a member of the Bethnal Green Mob asks the question, "What is it between Harry and Hammond?" A question that is never properly answered.

In the mission Aboard the Sol Vita, Harry taunts Mark by saying "[Suzie] gave up singing for a piece of shit like you (Hammond)". This implies that Harry knew Suzie before Mark did, and killed her intentionally due to her choosing Mark over him. This could be why Harry hates Mark more than everyone else.